Thionyl Chloride → HCID 67548869, compound

HRID 43568Notes

Reaction equation

HRID 43568 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:33]=[CH:32][C:20]2[N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:23][O:24][C:19]=2[CH:18]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][C:17]2[CH:33]=[CH:32][C:20]3[N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:22][CH2:23][O:24][C:19]=3[CH:18]=2)=[O:11])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 675497521171126-84-3

Product 1

HCID 67548869HCID 67548869, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (100 mg, 0.59 mmol), thionyl chloride (5 mL), pyridine (10 mL) and tert-butyl 7-amino-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate obtained in Example (95b) (0.3 g, 1.20 mmol), to obtain 0.13 g of the title compound as a pale yellow solid (56%).

Sources & evidence

ORD record
ord-d507c3fe824645938cc2a8f05b41a84b
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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